ChemFOnt: Showing chemical card for Tartaric acid (CFc000000763)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:15 UTC

Chemfont ID

CFc000000763

Molecule Identification

Common Name

Tartaric acid

Definition

Tartaric acid is a white crystalline organic acid. It occurs naturally in many plants, particularly grapes and tamarinds, and is one of the main acids found in wine. It is added to other foods to give a sour taste, and is used as an antioxidant. Salts of tartaric acid are known as tartrates. It is a dihydroxy derivative of dicarboxylic acid. Tartaric acid is a muscle toxin, which works by inhibiting the production of malic acid, and in high doses causes paralysis and death. The minimum recorded fatal dose for a human is about 12 grams. In spite of that, it is included in many foods, especially sour-tasting sweets. As a food additive, tartaric acid is used as an antioxidant with E number E334, tartrates are other additives serving as antioxidants or emulsifiers. Naturally-occurring tartaric acid is chiral, meaning that it has molecules that are non-superimposable on their mirror-images. It is a useful raw material in organic chemistry for the synthesis of other chiral molecules. The naturally occurring form of the acid is L-(+)-tartaric acid or dextrotartaric acid. The mirror-image (enantiomeric) form, levotartaric acid or D-(-)-tartaric acid, and the achiral form, mesotartaric acid, can be made artificially. Tartarate is believed to play a role in inhibiting kidney stone formation. Most tartarate that is consumed by humans is metabolized by bacteria in the gastrointestinal tract -- primarily in the large instestine. Only about 15-20% of consumed tartaric acid is secreted in the urine unchanged. Tartaric acid is a biomarker for the consumption of wine and grapes (PMID:24507823 ). Tartaric acid is also a fungal metabolite, elevated levels in the urine (especially in children) may be due to the presence of yeast (in the gut or bladder). It can be produced by Agrobacterium, Nocardia, Rhizobium, Saccharomyces as well (PMID:7628083 ) (https://link.springer.com/article/10.1023/A:1005592104426). High levels of tartaric acid have been found in autistic children. In adults, tartaric acid may be due to the consumption of wine (https://www.greatplainslaboratory.com/articles-1/2015/11/13/candida-and-overgrowth-the-problem-bacteria-by-products) (PMID:15738524 ; PMID:24507823 ; PMID:7628083 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+)-(R,R)-Tartaric acid	ChEBI
(+)-L-Tartaric acid	ChEBI
(+)-Tartaric acid	ChEBI
(+)-Weinsaeure	ChEBI
(2R,3R)-2,3-Dihydroxybernsteinsaeure	ChEBI
(2R,3R)-2,3-Dihydroxysuccinic acid	ChEBI
(2R,3R)-Tartaric acid	ChEBI
(R,R)-(+)-Tartaric acid	ChEBI
(R,R)-Tartaric acid	ChEBI
L(+)-TARTARIC ACID	ChEBI
L-Threaric acid	ChEBI
Rechtsweinsaeure	ChEBI
Weinsteinsaeure	ChEBI
(R,R)-Tartrate	Kegg
L-Tartaric acid	Kegg
Tartrate	Kegg
2,3-Dihydroxybutanedioic acid	Kegg
(+)-(R,R)-Tartarate	Generator
(+)-L-Tartarate	Generator
(+)-Tartarate	Generator
(2R,3R)-2,3-Dihydroxysuccinate	Generator
(2R,3R)-Tartarate	Generator
(R,R)-(+)-Tartarate	Generator
(R,R)-Tartarate	Generator
L(+)-TARTARate	Generator
L-Threarate	Generator
(R,R)-Tartric acid	Generator
L-Tartarate	Generator
Tartric acid	Generator
2,3-Dihydroxybutanedioate	Generator
Tartarate	Generator
Aluminum tartrate	HMDB
Ammonium tartrate	HMDB
Potassium tartrate	HMDB
Seignette salt	HMDB
Sodium ammonium tartrate	HMDB
Stannous tartrate	HMDB
Tartaric acid, calcium salt, (R-r,r)-isomer	HMDB
Calcium tartrate tetrahydrate	HMDB
Sodium tartrate	HMDB
Tartaric acid, ((r,r)-(+-))-isomer	HMDB
Tartaric acid, monoammonium salt, (R-(r,r))-isomer	HMDB
(R,r)-(+-)-2,3-dihydroxybutanedioic acid, monoammonium monosodium salt	HMDB
MN(III) tartrate	HMDB
Calcium tartrate	HMDB
Tartaric acid, (R-(r,r))-isomer	HMDB
Sodium potassium tartrate	HMDB
Tartaric acid, (r,s)-isomer	HMDB
Tartaric acid, (S-(r,r))-isomer	HMDB
Tartaric acid, ammonium sodium salt, (1:1:1) salt, (r,r)-(+-)-isomer	HMDB
(+)-(2R,3R)-Tartaric acid	HMDB
(1R,2R)-1,2-Dihydroxyethane-1,2-dicarboxylic acid	HMDB
(2R,3R)-2,3-Dihydroxybutanedioate	HMDB
(2R,3R)-2,3-Dihydroxybutanedioic acid	HMDB
(2R,3R)-2,3-Tartaric acid	HMDB
1,2-Dihydroxyethane-1,2-dicarboxylic acid	HMDB
2,3-Dihydroxy-succinate	HMDB
2,3-Dihydroxy-succinic acid	HMDB
2,3-Dihydroxysuccinic acid	HMDB
D-a,b-Dihydroxysuccinic acid	HMDB
D-Tartaric acid	HMDB
Dextrotartaric acid	HMDB
L-(+)-Tartaric acid	HMDB
Natural tartaric acid	HMDB
TAR	HMDB
Threaric acid	HMDB
TLA	HMDB
Weinsaeure	HMDB
(2R,3R)-(+)-Tartaric acid	HMDB
Dihydroxysuccinic acid	HMDB
Tartaric acid	HMDB

Chemical Formula

C₄H₆O₆

Average Molecular Weight

150.0868

Monoisotopic Molecular Weight

150.016437924

IUPAC Name

(2R,3R)-2,3-dihydroxybutanedioic acid

Traditional Name

L(+)-tartaric acid

CAS Registry Number

87-69-4

SMILES

O[C@H]([C@@H](O)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C4H6O6/c5-1(3(7)8)2(6)4(9)10/h1-2,5-6H,(H,7,8)(H,9,10)/t1-,2-/m1/s1

InChI Key

FEWJPZIEWOKRBE-JCYAYHJZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Sugar acids and derivatives

Alternative Parents

Substituents

Sugar acid
Short-chain hydroxy acid
Beta-hydroxy acid
Fatty acid
Monosaccharide
Hydroxy acid
Dicarboxylic acid or derivatives
Alpha-hydroxy acid
Secondary alcohol
1,2-diol
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

tartaric acid (CHEBI:15671 )

Functional Ontology

Physiological effect

Health effect

Cancer

Cancer (HMDB: HMDB0000956)

Respiratory system disorder

Pulmonary disorder

Lung Cancer (HMDB: HMDB0000956)

Adipose tissue (HMDB: HMDB0000956)
Adipose tissue (HMDB: HMDB0000956)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Cell

Hematocyte

Platelet (HMDB: HMDB0000956)

Organ

Prostate (HMDB: HMDB0000956)

Excreta

Biofluid or Excreta

Urine (PMID: 22157537)
Feces (PMID: 25670064)

Cellular substructure

Cytoplasm (HMDB: HMDB0000956)
Extracellular (HMDB: HMDB0000956)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000956)

Source

Exogenous

Exogenous (HMDB: HMDB0000956)

Food

Food (HMDB: HMDB0000956)

Beverage

Fermented beverage

Fortified wines

Port wine (FooDB: FOOD00630)

Alcoholic beverage

Red wine (HMDB: HMDB0000956)

Fig (FooDB: FOOD00081)

Grapes (HMDB: HMDB0000956)

Pome

Quince (FooDB: FOOD00069)

Vegetable

Fruit vegetable

Avocado (FooDB: FOOD00130)
Garden tomato (var.) (FooDB: FOOD00173)

Root vegetable

Leaf vegetable

Lettuce (FooDB: FOOD00095)

Tuber

Potato (FooDB: FOOD00175)

Onion-family vegetable

Garden onion (FooDB: FOOD00006)

Herb and spice

Spice

Herb

Dandelion (FooDB: FOOD00181)
Sorrel (FooDB: FOOD00164)
Fennel (FooDB: FOOD00082)
Parsley (FooDB: FOOD00131)
Roselle (FooDB: FOOD00447)

Oilseed crop

Sunflower (FooDB: FOOD00086)

Cereal and cereal product

Cereal

Corn (FooDB: FOOD00205)
Oat (FooDB: FOOD00022)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Synthetic

Personal care products

Personal care products (HMDB: HMDB0000956)

Endogenous

Plant

Plant (HMDB: HMDB0000956)
Coffea (HMDB: HMDB0000956)

Microbe

Fungi

Yeast

Yeast (HMDB: HMDB0000956)

Saccharomyces (HMDB: HMDB0000956)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Inner Membrane Transport (PathBank: SMP0121270)
Glycolate and Glyoxylate Degradation II (PathBank: SMP0122218)

Role

Industrial applicationIndirect biological role

Carcinogen (HMDB: HMDB0000956)

Biological role

Acidifier (HMDB: HMDB0000956)
Irritant (HMDB: HMDB0000956)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	161 g/L	ALOGPS
logP	-1.3	ALOGPS
logP	-1.8	ChemAxon
logS	0.03	ALOGPS
pKa (Strongest Acidic)	2.72	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	115.06 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	26.21 m³·mol⁻¹	ChemAxon
Polarizability	11.33 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon